1-[(n-hex-1-ylamino)ethyl]-1,1-bisphosphonic acid

ID: ALA259192

PubChem CID: 19689034

Max Phase: Preclinical

Molecular Formula: C8H21NO6P2

Molecular Weight: 289.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCNCC(P(=O)(O)O)P(=O)(O)O

Standard InChI:  InChI=1S/C8H21NO6P2/c1-2-3-4-5-6-9-7-8(16(10,11)12)17(13,14)15/h8-9H,2-7H2,1H3,(H2,10,11,12)(H2,13,14,15)

Standard InChI Key:  QDLXIUDMSHZYCG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 16  0  0  0  0  0  0  0  0999 V2000
   11.3071    2.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3071    1.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5926    3.2221    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.0216    3.2221    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.7279    3.6438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8771    3.6346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0048    3.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1812    2.5070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4392    2.5106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6059    3.9347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5926    1.5721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5926    0.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8781    0.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8781   -0.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1637   -0.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1637   -1.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4492   -2.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  9  1  0
  4  5  1  0
  4 10  2  0
  1  3  1  0
  2 11  1  0
  3  6  2  0
 11 12  1  0
  1  2  1  0
 12 13  1  0
  3  7  1  0
 13 14  1  0
  1  4  1  0
 14 15  1  0
  3  8  1  0
 15 16  1  0
 16 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA259192

   [2-(Hexylamino)ethane-1,1-Diyl]bis(Phosphonic Acid)

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 289.21

Molecular Weight (Monoisotopic): 289.0844

AlogP: 0.84

#Rotatable Bonds: 9

Polar Surface Area: 127.09

Molecular Species: ZWITTERION

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.71

CX Basic pKa: 11.31

CX LogP: -2.06

CX LogD: -4.41

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.31

Np Likeness Score: 0.20

References

1. Szajnman SH, García Liñares GE, Li ZH, Jiang C, Galizzi M, Bontempi EJ, Ferella M, Moreno SN, Docampo R, Rodriguez JB..  (2008)  Synthesis and biological evaluation of 2-alkylaminoethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase.,  16  (6): [PMID:18096393] [10.1016/j.bmc.2007.12.010]

2. Rosso VS, Szajnman SH, Malayil L, Galizzi M, Moreno SN, Docampo R, Rodriguez JB..  (2011)  Synthesis and biological evaluation of new 2-alkylaminoethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase.,  19  (7): [PMID:21419634] [10.1016/j.bmc.2011.02.037]

3. Aripirala S, Szajnman SH, Jakoncic J, Rodriguez JB, Docampo R, Gabelli SB, Amzel LM..  (2012)  Design, synthesis, calorimetry, and crystallographic analysis of 2-alkylaminoethyl-1,1-bisphosphonates as inhibitors of Trypanosoma cruzi farnesyl diphosphate synthase.,  55  (14): [PMID:22715997] [10.1021/jm300425y]

4. Ferrer-Casal M, Li C, Galizzi M, Stortz CA, Szajnman SH, Docampo R, Moreno SN, Rodriguez JB..  (2014)  New insights into molecular recognition of 1,1-bisphosphonic acids by farnesyl diphosphate synthase.,  22  (1): [PMID:24300918] [10.1016/j.bmc.2013.11.010]

5. Galaka T, Falcone BN, Li C, Szajnman SH, Moreno SNJ, Docampo R, Rodriguez JB..  (2019)  Synthesis and biological evaluation of 1-alkylaminomethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii.,  27  (16): [PMID:31296439] [10.1016/j.bmc.2019.07.004]

Source

Source(1):

• Scientific Literature